REACTIONS OF TRIARYLSULFONIUM SALTS WITH BASES

Triphenylsulfonium and tri-p-tolylsulfonium fluoroborate, iodide, bromide, and chloride salts have been prepared and subjected to reaction with sodium methoxide in methanol solution. In all cases, a mixture of aromatic hydrocarbons, biaryls, methyl aryl ethers, diaryl sulfides, and products of relatively high molecular weight were obtained. However, the molar ratios of these products differed markedly from one system to another. An interpretation of these results and of those of the reactions of some of the same triarylsulfonium salts with other sodium alkoxides is offered in terms of competing free-radical and aromatic bimolecular nucleophilic substitution reactions. Preliminary examinations of the thermal decomposition of triphenylsulfonium hydroxide and of the photolysis of triphenylsulfonium salts have also been made. © 1969, American Chemical Society. All rights reserved.